The accurate and reliable estimation of travel time based on point detector data is needed to support Intelligent Transportation System (ITS) applications. It has been found that the quality of travel time estimation is a function of the method used in the estimation and varies for different traffic conditions. In this study, two hybrid on-line travel time estimation models, and their corresponding off-line methods, were developed to achieve better estimation performance under various traffic conditions, including recurrent congestion and incidents. The first model combines the Mid-Point method, which is a speed-based method, with a traffic flow-based method. The second model integrates two speed-based methods: the Mid-Point method and the Minimum Speed method. In both models, the switch between travel time estimation methods is based on the congestion level and queue status automatically identified by clustering analysis. During incident conditions with rapidly changing queue lengths, shock wave analysis-based refinements are applied for on-line estimation to capture the fast queue propagation and recovery. Travel time estimates obtained from existing speed-based methods, traffic flow-based methods, and the models developed were tested using both simulation and real-world data. The results indicate that all tested methods performed at an acceptable level during periods of low congestion. However, their performances vary with an increase in congestion. Comparisons with other estimation methods also show that the developed hybrid models perform well in all cases. Further comparisons between the on-line and off-line travel time estimation methods reveal that off-line methods perform significantly better only during fast-changing congested conditions, such as during incidents. The impacts of major influential factors on the performance of travel time estimation, including data preprocessing procedures, detector errors, detector spacing, frequency of travel time updates to traveler information devices, travel time link length, and posted travel time range, were investigated in this study. The results show that these factors have more significant impacts on the estimation accuracy and reliability under congested conditions than during uncongested conditions. For the incident conditions, the estimation quality improves with the use of a short rolling period for data smoothing, more accurate detector data, and frequent travel time updates.